The rise of Henry VII: how a life of cheating death prepared him for the throne as the first Tudor king

Francis Bacon, writing in the early 17th century, remarked that Henry was “a dark prince, and infinitely suspicious”, who would admit no one “to his power or to his secrets”. There is an element of truth in Bacon’s judgment that Henry became “lost in a wood of suspicions”.

• Read more | Henry VII: the greatest pretender

Henry’s wary nature is typically attributed to his shaky claim to the throne. The first Tudor monarch was unable to escape the taunt that he was a usurper with no right to call himself king. In fact, his renowned paranoia was the inevitable consequence of a traumatic youth – a trait ingrained long before he harboured ambitions to wear a crown.

If we delve deeper into Henry’s background, we can draw a fuller picture of one of our most circumspect of monarchs – one that might elicit sympathy for a long misunderstood king.

Growing up with the enemy

Henry was not born to rule. Indeed, he was born far from the throne, both figuratively and literally. The son of Margaret Beaufort, an English heiress of royal descent, and a half-Welsh, half-French earl named Edmund Tudor, Henry was born in Pembroke Castle on 28 January 1457. It was an inopportune moment to arrive in the world: civil war was brewing between the rival houses of York and Lancaster, remembered today as the Wars of the Roses.

Henry was related on both sides of his family tree to the beleaguered Lancastrian king Henry VI, who was both his maternal cousin and his paternal half-uncle. He never knew his father, Edmund Tudor, who died three months before Henry was born.

Edmund, who had been engaged in conflict with a Yorkist faction led by William Herbert, perished in uncertain circumstances in Carmarthen in November 1456, having not long been released from a Yorkist prison. In any case, Margaret was just 13 years old when she gave birth to Henry, and the baby’s welfare was entrusted to his uncle Jasper Tudor, Earl of Pembroke.

A series of battles between 1459 and 1461 ultimately displaced the Lancastrians from the English throne. Henry’s grandfather, Owen Tudor, was executed and his uncle Jasper was forced into penurious exile. At just four years old, Henry’s wardship was sold by the new Yorkist king, Edward IV, to none other than Herbert, the avowed enemy of the Tudors, who had been closely implicated in the death of the boy’s father, Edmund, just five years earlier.

Being just a child, Henry had no input in this decision. He spent the next decade living with the Herberts at Raglan Castle in Monmouthshire, on the Welsh border. There he enjoyed a stable life and a solid education.

War, however, continued to rear its ugly head. At the battle of Edgcote in July 1469, Lord Herbert fought rebels loyal to Edward IV’s wayward brother George, Duke of Clarence, and cousin Richard Neville, better known as Warwick ‘the Kingmaker’. Herbert, whose side lost the battle, was captured and beheaded. It is possible Henry was himself present at this engagement; if so, it would have been a horrifying first experience of warfare.

When Clarence and Warwick helped restore the Lancastrian king Henry VI to the throne the following year, though, the door was opened for the young Henry Tudor to be reunited with Jasper, the uncle he barely knew.

Edward IV targets Henry Tudor

The Lancastrian resurgence proved short-lived: in May 1471, Edward IV wrested back his crown in battle then, over the days that followed, ruthlessly eliminated the flower of Lancaster. Among the dead were Henry VI; his son, Prince Edward of Westminster; and his cousins Edmund and John Beaufort.

As a consequence of this bloodletting, the previously lightly regarded Henry Tudor, still just 14 years old, was suddenly in the Yorkist crosshairs. As one foreign ambassador remarked, Edward IV was determined to “crush the seed” of Lancastrianism.

Henry was at Chepstow with Jasper when they were set upon by a Yorkist soldier sent by the king to seize them. His uncle was able to turn the tables and kill this would-be captor but, conscious that reinforcements would soon appear, the two Tudors quickly set off across the wilds of south Wales. At Jasper’s seat, Pembroke, they were besieged for eight tense and terrifying days before escaping to the nearby coastal fort of Tenby.

Uncle and nephew scrambled through a network of underground tunnels down to the harbour, where they hopped into a waiting vessel. Their departure marked the start of 14 years of exile for Henry. Tossed by a storm, the Tudors eventually made landfall in Brittany. There they received the protection of Duke Francis II.

Henry's life in exile

When Edward IV discovered that Henry had escaped, he sought to manipulate Francis’s very real fears of being conquered by the acquisitive French crown. Brittany and Yorkist England were allies, and Edward expected Francis to surrender the Tudors at once.

But Francis hesitated. If he turned over Henry, he would have no bargaining chip with which to extract military or financial support from the English, who were equally keen that the Bretons didn’t deliver the Tudors to the French. Hampered by geopolitics, Francis instead swore “upon his honour” to protect his guests. Hence the disconcerted Henry found himself a pawn in a fluid Anglo-French-Breton diplomatic tussle; like a ship in a tempest, his fate lay outside his control.

For much of the next dozen years, Henry was closely observed, his movement curtailed and his servants heavily vetted. According to a contemporary observation by the Frenchman Philippe de Commines, the Tudors were treated “very handsomely for prisoners”, but it was clear that they were vulnerable to the whims of others.

Henry found himself a pawn in a fluid Anglo-French-Breton diplomatic tussle; like a ship in a tempest, his fate lay outside his control

This became evident five years into Henry’s Breton exile. In early 1476, Edward IV sought once more to get his hands on this evasive Lancastrian ally who remained tantalisingly out of his grasp. An embassy was sent across the Channel armed with chests of gold, hoping to persuade the Bretons to release their Tudor guest. Duke Francis’s resolve was weakened, and he “committed the sheep to the wolf”, handing Henry to Edward’s delegation.

The jubilant English envoys decamped to Saint-Malo, ready for the voyage back to their awaiting king. Still just 19, Henry likely viewed the ships in the harbour with trepidation, knowing that, as “the only imp” of Henry VI’s blood still living, he was being “carried to his death”.

So, at the final moment, Henry faked an illness. This provided an opportunity for the Bretons to change their mind, and in the confusion that ensued he managed to slip away from his captors, fleeing through the narrow streets to claim sanctuary in the cathedral. When the Englishmen tried to force their way in, they were beaten back by the outraged local populace and returned home empty handed.

Rise of Richard III

The next six years of Henry’s exile passed with little incident, living once more at the Breton court under the aegis of a contrite duke. For much of this time, Henry’s mother, Margaret Beaufort, worked hard to convince a mellowing Edward IV to permit her son to return home – and not to the chopping block.

By June 1482 she had wrested a draft pardon from Edward, which stipulated that Henry could return provided he bend the knee to the Yorkist king. He would be restored to the earldom of Richmond, and there was even a potential marriage to Edward’s eldest daughter, Elizabeth of York, on the cards.

But on 9 April 1483, before the negotiations could be concluded, Edward IV died. Within weeks the deceased king’s brother had orchestrated a coup to become Richard III.

The Yorkist court was bitterly divided between those who accepted the sidelining of Edward’s sons and those who didn’t. And when rumours spread that Richard’s nephews – popularly known today as the princes in the Tower – had been put to death, dismay manifested into outright rebellion.

• Read more | Did Richard III really kill the Princes in the Tower?

Concerned that Richard seemed unwilling to honour the pardon Edward IV had drafted for Henry, Margaret Beaufort now extended the hand of friendship to the princes’ grief-stricken mother, Elizabeth Woodville. The two women arranged to put past differences behind them to take down a common foe. The Duke of Buckingham – who himself had a royal claim – was persuaded to abandon his erstwhile ally, Richard, and lead the crusade.

Buckingham roused his tenants in October 1483, intending to link up with the Woodville contingent and an invading Henry Tudor. The uprising, however, proved farcical. Buckingham was captured with ease, and was executed soon afterwards. The Woodvilles were scattered, and Henry never even succeeded in making landfall in England.

The upshot of Buckingham’s death, combined with the belief that the Yorkist princes had been killed, was that there now remained only one realistic challenger for Richard’s crown: Henry Tudor.

Henry as heir to the throne

There is no evidence from before the end of 1483 that Henry or his mother had any aspirations for him to be king. And he was regarded by one foreign contemporary, Philippe de Commines, as a “person of no power, and one who had been long prisoner” who was “not the next heir to the crown”. Even so, Henry saw an opportunity – and seized it.

On Christmas Day 1483, Henry made a solemn promise to English rebels gathered before him in St Peter’s Cathedral, Rennes. If they sponsored his unlikely bid to be king, he would return their seized estates and offices. To further bind the Yorkist element to his cause, he swore to marry Elizabeth of York and symbolically unite the two warring royal houses. It was a bold gambit – but it paid off: the rebels pledged their fealty “as though he had already been created king”.

This marked an astonishing turnaround in Tudor fortunes. Now regarded by Richard III as “the king’s great rebel and traitor”, Henry’s task was daunting. He spent the first few months of 1484 trying to persuade Duke Francis of Brittany to fund a fresh enterprise against the English king, but was himself nearly outmanoeuvred by a wily Richard.

When Francis was taken ill, Richard sent across another embassy to deal with the Breton treasurer, Pierre Landais. Seeking personal enrichment, Landais promised to have an oblivious Henry seized and handed over. Fortunately for Henry, the Tudor camp had a spy in Richard’s council, and a messenger swiftly travelled to Brittany to warn Henry of his impending betrayal.

To further bind the Yorkist element to his cause, he swore to marry Elizabeth of York and symbolically unite the two warring royal houses. It was a bold gambit – but it paid off

Through necessity, the young Tudor had grown into a cautious adult, and took this news gravely. He summoned a few trusted figures to his side, and hatched yet another escape plan. He had already made two improbable flights during his lifetime: first as a 14-year-old in Tenby and again as a 19-year-old in Saint-Malo. Now, aged 27, he looked to complete a third.

At some point in September 1484, Henry departed his court-in-exile under the pretence of visiting an acquaintance. Just a few miles into his journey, Henry and his companions left the road. He quickly changed into the clothes of a servant and, suitably disguised, rode hard for the French border.

When they realised that something was afoot, the Bretons sent out a search party to bring Henry back. Stopping only briefly to water his exhausted horse, Henry made it into France with just an hour to spare. Once again, he had completed a remarkable escape.

Once the French discovered that Henry was on their turf, they immediately welcomed him to court, where he was treated with every courtesy. More importantly – and for their own ends – the French crown publicly sponsored Henry’s campaign to “recover the Kingdom of England”, and began to source funding and soldiers.

The path to Bosworth Field

Richard III was outraged by this development, and rued his failure to get his hands on Henry. On 7 December 1484, the king issued a scathing proclamation – a masterful exercise in propaganda, lashing out at the “rebels and traitors” who had taken as their captain a man of “ambitious and insatiable covetousness [with] no manner, interest, right or colour” to his crown.

All, Richard thundered, had not only forsaken their rightful king and natural country, but were murderers, adulterers and extortioners, moral delinquents who would inflict great harm on the English people if successful in their venture. Richard expected all “good and true Englishmen” to remain loyal.

Henry and his supporters persevered, however. Having secured a series of personal loans from a number of merchants to bolster his war chest, by the summer of 1485 the would-be king was ready to set sail. He led a modest force largely comprising French mercenaries and a few hundred English rebels with nothing to lose.

• Read more | Bosworth: the dawn of the Tudors

On 1 August 1485, Henry stepped onto a ship moored in Harfleur harbour. As he awaited a favourable wind to take him across the Channel to his uncertain fate, he may have reflected on his life to this point – and his repeated brushes with death. Removed from his family as a child, he had possibly witnessed the beheading of his guardian, and been forced to flee for his life on more than one occasion while still in his teens.

As a claimant to the English throne, his life was still in constant peril. It is easy to picture Henry on the deck of his ship, staring out to sea, vowing that – if this unlikely quest proved successful – he would never again be a pawn in others’ games.

History has adjudged Henry a king racked with suspicions; a trait that left him unloved and unmourned at death. His path to the throne, however, had taught him to be wary of both friend and foe. His court biographer, Polydore Vergil, wrote of Henry that “his mind was brave and resolute and never, even at the moments of the greatest danger, deserted him”.

Life experience had taught Henry to be guarded. Far from a weakness, it was an attribute that served him well as king. He was suspicious, yes, but successful – and a true survivor.

Nathen Amin is an author specialising in the reign of Henry VII. His new book is Son of Prophecy: The Rise of Henry Tudor (Amberley, 2024)

This article was first published in the September 2024 issue of BBC History Magazine